Hydrazine hydrate (1:1) → HCID 178456016, compound

HRID 1655724Notes

Reaction equation

HRID 1655724 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([C@@H:21]([NH:28][C:29]([C@H:31]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:32][C:33]([O:35]CC)=O)=[O:30])[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[CH2:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[NH2:46][NH2:47]>CO>[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([C@@H:21]([NH:28][C:29]([C@H:31]([CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:32][C:33]([NH:46][NH2:47])=[O:35])=[O:30])[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:15])[CH3:16])[CH:12]=[CH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178456017HCID 178456017, compound

Product 1

HCID 178456016HCID 178456016, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.164 mmol) of ethyl (R)-3-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]-4-phenylbutyrate were stirred at room temperature for 3 hours in a solution of 30% hydrazine hydrate in methanol. Thereafter, the reaction mixture was evaporated and the residue was chromatographed on silica gel with a 14:1:0.1 mixture of methylene chloride, methanol and ammonia. Crystallization of the crude product from methanol/methylene chloride/ether yielded (R)-3-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]-carbamoyl]4-phenylbutyrohydrazide as white crystals, melting point 109°.

Workup

  1. customThereafter, the reaction mixture was evaporated
  2. customthe residue was chromatographed on silica gel with a 14:1:0.1 mixture of methylene chloride, methanol and ammonia
  3. customCrystallization of the crude product from methanol/methylene chloride/ether

Sources & evidence

ORD record
ord-53349505dc1b4f96ac01777962498205
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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